US3383236A - Continuous pharmaceutical film coating process - Google Patents

Continuous pharmaceutical film coating process Download PDF

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Publication number
US3383236A
US3383236A US360772A US36077264A US3383236A US 3383236 A US3383236 A US 3383236A US 360772 A US360772 A US 360772A US 36077264 A US36077264 A US 36077264A US 3383236 A US3383236 A US 3383236A
Authority
US
United States
Prior art keywords
coating
tablets
methyl cellulose
continuous
film
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US360772A
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English (en)
Inventor
Normand E Brindamour
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Priority to US360772A priority Critical patent/US3383236A/en
Priority to IL22778A priority patent/IL22778A/xx
Priority to BR166503/65A priority patent/BR6566503D0/pt
Priority to DE19651492029 priority patent/DE1492029A1/de
Priority to GB5354/65A priority patent/GB1059508A/en
Priority to NL6502190A priority patent/NL6502190A/xx
Priority to FR7501A priority patent/FR1455065A/fr
Priority to BE661581D priority patent/BE661581A/xx
Priority to NO157671A priority patent/NO117494B/no
Priority to SE04965/65A priority patent/SE352531B/xx
Priority to ES0312253A priority patent/ES312253A1/es
Application granted granted Critical
Publication of US3383236A publication Critical patent/US3383236A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

Definitions

  • This invention relates to novel compositions and methods for the production of coated solid dosage units containing pharmaceutical ingredients.
  • the coating of solid dosage units containing pharmaceutical compositions is well known.
  • a water repellent resinous material such as zein, shellac, cellulose acetate phthalate, or fatty material, which forms a protective barrier against the moisture later applied.
  • subcoating materials such as gelatin and acacia, which materials are dusted when wet with powders. This subcoating is required in the sugar process to round out the edges of the dosage unit prior to the application of a basically plain syrup which is deposited as a crystalline layer of sugar.
  • the coated dosage unit is finally colored and polished. The process is time consuming, requiring from two to six days, and is also expensive.
  • Thin film coatings have been described wherein a stop and go process of application of substances, such as the cellulose derivatives, the polyethylene glycols, the prolamines, and the acetylated monoglycerides, or mixtures and modifications of the above were applied.
  • substances such as the cellulose derivatives, the polyethylene glycols, the prolamines, and the acetylated monoglycerides, or mixtures and modifications of the above were applied.
  • Such applications have been variously described in (1) Drug Standards, p. 29, January-February 1958; (2) US. Patent No. 2,881,085; (3) Drug Cosmetic Inds. 75, p. 466; and (4) J. Amer. Pharm. Assoc, Sci. Ed. 43, 433 (1954), the disclosures thereof being incorporated herein by reference and made a part hereof.
  • the lengthy process of the sugar coatings combined with the large build-up in tablet size suggests room for improvement.
  • the film coating processes described in the literative are those wherein the film is applied in charges by pouring a solution of the film former onto a rolling bed of tablets. As the tablets rotate, the material is distributed over the surface, thereof, and there is a material transfer from tablet to tablet. In a few minutes time usually aided by the application of heat, the solvents evaporate leaving a random deposition of film on the tablets. The cycle is then repeated until the coating is judged to be satisfactory. This is what is known in the trade as a stop and go process. In the above process, some tablets are actually overwet by the film coating solution and a continuous homogeneous film is dependent upon the transfer of film from tablet to tablet, and therefore a film of uniform thickness and composition is difiicult to attain.
  • a continuous non-toxic film coating may be produced on shaped cores containing pharmaceutical ingredients by the deposition thereon of a composition consisting essentially of a continuous film of a compound selected from the class consisting of methyl cellulose and hydroxypropyl methyl cellulose.
  • Methyl cellulose is essentially the dimethyl ether of cellulose, and hydroxypropyl methyl cellulose constitutes methyl cellulose in which varying ratios of propylene glycol ether substiuttion to methoxyl substitution exist.
  • the film forming composition is applied to the shape cores containing pharmaceutical ingredients by the process of this invention which comprises the steps of (l) establishing a rolling bed of shaped dosage units of a pharmaceutical ingredient, (2) continuously spraying said dosage units with a solution of a compound selected from the class consisting of methyl cellulose and hydroxypropyl methyl cellulose in substantially equal amounts of ethanol and chloroform in an atomized state, (3) continuously evaporating said ethanol and chloroform from said sprayed dosage units at a rate such that said dosage units maintain a substantially dry appearance and wherein there is materially no transfer of film per se or of film forming solution from tablet to tablet, and (4) continuing the simultaneous rolling, spraying and evaporating, and controlling the relative spray rate and evaporation in such a manner as to prevent transfer from tablet to tablet until a continuous film of the desired thickness and quality has been established on the dosage unit.
  • composition of the present invention it is possible to use a conventional pear shaped rotating coating pan and to spray it on the tumbling tablets.
  • best results are obtained if one uses the specifically designed rotating coating pan and its associated equipment which are described in my patent application Ser. No.
  • the coating process being novel in its concept and new in its application is an integral part of the invention.
  • this novel process it becomes necessary to achieve a fairly high degree of turbulence in the tablet mass and it is a requisite that each tablet pass beneath the spray in several positions.
  • the film is transferred from tablet to tablet so agitation need not be as severe.
  • the upper limit of turbulence is that which causes abrasion and breakage of the tablet.
  • the weight of the tablet bed upon the coating aids in molding the film into a smooth continuous coating, but is not a requisite in all cases and other methods of imparting movement to the tablets could be used.
  • the pressure of the spray is sufficient to noticeably indent a portion of the agitated tablet mass, an action which significantly contributes to the mixing of the tablets since it involves a change of direction in a portion of the mass.
  • the preferred method of obtaining the requisite turbulence is the rolling of the tablets in a coating pan equipped with an air supply and exhaust.
  • the most important factors contributing to the process are the particle size of the suspended particles and spray droplet and the impact velocity. These are controlled by regulating the orifice sizes of both the air and fluid nozzles, the pressure on the atomized material which flows through the fluid orifice, and the pressure of the atomizing air if such is used. They are also controlled by regulating the viscosity and solids content of the coating composition, the number of nozzles, the spray distance, the size and shape of the spray pattern, the direction of the spray in relation to the travel of the tablets, and the spray angle. The number of nozzles does not vary directly as the weight of the pan load.
  • the average drop diameter is 18 microns for the process recommended which produces the type of coating desired. However, if a small change in drop diameter is desired, the following equation (Kirk-Othmer, Encyclopedia of Chemical Technology) can be used as a guide toward adjusting flow ratios and the physical properties of the spray solution:
  • the drying rate can be controlled by regulating the temperature and volume of the drying air and by regulating the rate, direction, and volume of the exhaust air.
  • the air can be directed to flow through or over the bed in any direction by diverse mechanical means.
  • the particle size of the suspended particles and the viscosity of the coating composition are rigidly controlled.
  • EXAMPLE 1 60.75 liters of anhydrous ethanol (SD3A) were placed into a stainless steel container equipped with a high speed air-driven agitator. While stirring, 2.673 kilograms of hydroxypropyl methyl cellulose, N.F., 50 cps., were added slowly to avoid clumping. Then there was added in order, 0.668 kilogram of diethyl phthalate and 60.75 liters of chloroform U.S.P., the contents then being mixed until the hydroxypropyl methyl cellulose was dissolved.
  • SD3A anhydrous ethanol
  • Coating procedure 40.5 kilograms of compressed cores containing 0.25 gm. l-a-methyldopa each were placed in a 42 inch stainless steel coating pan equipped with an air blower and exhaust system. The exhaust was turned on and drying air was directed toward the bottom of the tablet bed and adjusted to a temperature of approximately 190 F. The pan was then rotated at approximately 19 rpm, which caused the cores to take on a uniformly tumbling motion.
  • a manifold of 4 No. 2050 fluid nozzles (Spray Systems) equipped with a No. air nozzle and cleanout assembly was arranged to continuously coat the full area of the pan occupied by the cores. The previously prepared suspension was contained in a reservoir located ten inches above the manifold and fed by siphon to the nozzles.
  • EXAMPLE 2 75.25 liters of anhydrous ethanol (SD3A) were placed into a stainless steel container equipped with a high speed stainless steel, air-driven agitator. While stirring, 3.311 kilograms of hydroxypropyl methyl cellulose, N.F., 50 cps., were added to avoid clumping. Then there was added in order, 0.828 kilogram of diethyl phthalate and 75.25 liters of chloroform, U.S.P., the contents then being mixed until the hydroxypropyl methyl cellulose was dissolved.
  • SD3A anhydrous ethanol
  • Film Coating Suspension A was contained in a reservoir located ten inches above the manifold and fed by siphon to the nozzles. 25.00 liters of Film Coating Suspension A were sprayed from the nozzles using an atomizing air pressure of 46 p.s.i. pressure. They spray was directed at an angle to the face of the pan impinging to the left and in the opposite direction to the tablet flow. The average distance between the spray nozzles and the pan load was in the range of from about 7 to about 8 inches. The suspension flow rate was in the range of from about 0.225 to about 0.250 kilogram per minute, and the pan load was maintained at a temperature in the range of from about 28 C. to about 33 C. with the exhaust damper completely open.
  • EXAMPLE 3 20.0 liters of the following film coating suspension, prepared essentially in the manner of Example 1, were sprayed onto approximately 33.0 kilograms of compressed cores containing 50 mg. indomethacin in the manner of Example 1.
  • the resulting tablets had an opaque continuous film coating formed thereon, which coating took a high polish when tumbled in carnauba wax.
  • diethyl phthalate in the film coating composition of this invention is to provide the properties of a plasticizer, but such an ingredient is not critical to the effectiveness of the hydroxypropyl methyl cellulose without a plasticizer.
  • talc in the spraying solution is preferred for the reason that it prevents undue sticking of the cores to each other during the coating process.
  • non-toxic coloring agents disclosed in the above examples are only exemplary of the use of such coloring agents in the coating composition, and any compatible non-toxic coloring agent may be used effectively.
  • EXAMPLE 4 Coating solution: Amount Methyl cellulose, 25 c.p.s gm 4 Alcohol SD3A, anhydrous ml 100 Chloroform ml 100 FDC Yellow No. 3 gm 0.01
  • EXAMPLE 7 Coating solution: Amount Methyl cellulose, 25 c.p.s "gm-.. 6 Water ml 15 Dioxane ml 285 An intermittent spray with continuous application of hot drying air was successfully used to coat the tablets.
  • EXAMPLE l0 Coating solution Amount Methyl cellulose, 25 c.p.s gm 8 Alcohol, anhydrous ml 100 Chloroform ml 100 DC Yellow No. 11 gm 0.01
  • EXAMPLE 11 Coating solution: Amount Methyl cellulose, 15 c.p.s gm 10 Alcohol, anhydrous ml 100 Chloroform ml 100 Iron oxide brown gm 1 A continuous spray formed by 5 lbs. pressure on the coating solution was used with continuous application of hot drying air to successfully coat the tablets.
  • EXAMPLE 12 Coating solution: Amount Methyl cellulose, 25 c.p.s gm 4 Chloroform ml 100 Alcohol, anhydrous ml 100 TiO gm 0.5
  • EXAMPLE 13 Coating solution: Amount Methyl cellulose, 25 c.p.s gm 4 Alcohol, anhydrous ml 100 Chloroform ml 100 gHL... -5 FDC Yellow No. 5 gm 0.05
  • EXAMPLE 14 A 5,000 gram batch of 130 mg. tablets containing as an active ingredient amitriptyline hydrochloride, 25 mg., was successfully coated by spraying continuously with intermittent application of hot drying air the following solution:
  • EXAMPLE 17 Using the procedure and solution described in Example 14, a 5,000 gram batch of 130 mg. tablets containing as an active ingredient nor-amitriptyline hydrochloride, 25 mg., was successfully coated.
  • EXAMPLE 18 A 1,650 gm. batch of 130 mg. tablets containing as an active ingredient nor-amitriptyline hydrochloride, 10 mg, was successfully coated using the procedure described in Example 14 with the following solution:
  • a process for forming a continuous nontoxic film coating on a plurality of shaped pharmateutical ingredient containing cores the steps which comprise (1) establishing a continuous tumbling movement of said cores, (2) continuously spraying said moving cores with an atomized solution of a compound selected from the class consisting of hydroxypropyl methyl cellulose and methyl cellulose in a solvent mixture selected from the group consisting of ethanol-chloroform, methylene chloride-isopropanol, toluene-alcohol, carbon tetrachloride-isopropanol, and methanol-chloroform, the spraying solution being applied at a rate of 0.225 to 0.250 kg./min.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Preparation (AREA)
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US360772A 1964-04-17 1964-04-17 Continuous pharmaceutical film coating process Expired - Lifetime US3383236A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US360772A US3383236A (en) 1964-04-17 1964-04-17 Continuous pharmaceutical film coating process
IL22778A IL22778A (en) 1964-04-17 1965-01-14 Film-coated pharmaceutical compositions
BR166503/65A BR6566503D0 (pt) 1964-04-17 1965-01-26 Processo para a formacao de um revestimento de pelicula
DE19651492029 DE1492029A1 (de) 1964-04-17 1965-01-28 Dragierverfahren
GB5354/65A GB1059508A (en) 1964-04-17 1965-02-08 Coating tablets
NL6502190A NL6502190A (enrdf_load_stackoverflow) 1964-04-17 1965-02-22
FR7501A FR1455065A (fr) 1964-04-17 1965-03-01 Procédé d'enrobage et compositions de pellicule d'enrobage
BE661581D BE661581A (enrdf_load_stackoverflow) 1964-04-17 1965-03-24
NO157671A NO117494B (enrdf_load_stackoverflow) 1964-04-17 1965-04-13
SE04965/65A SE352531B (enrdf_load_stackoverflow) 1964-04-17 1965-04-14
ES0312253A ES312253A1 (es) 1964-04-17 1965-04-15 Procedimiento para formar un recubrimiento en forma de pelicula,para unidades de dosis farmaceuticas.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US360772A US3383236A (en) 1964-04-17 1964-04-17 Continuous pharmaceutical film coating process

Publications (1)

Publication Number Publication Date
US3383236A true US3383236A (en) 1968-05-14

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US360772A Expired - Lifetime US3383236A (en) 1964-04-17 1964-04-17 Continuous pharmaceutical film coating process

Country Status (11)

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US (1) US3383236A (enrdf_load_stackoverflow)
BE (1) BE661581A (enrdf_load_stackoverflow)
BR (1) BR6566503D0 (enrdf_load_stackoverflow)
DE (1) DE1492029A1 (enrdf_load_stackoverflow)
ES (1) ES312253A1 (enrdf_load_stackoverflow)
FR (1) FR1455065A (enrdf_load_stackoverflow)
GB (1) GB1059508A (enrdf_load_stackoverflow)
IL (1) IL22778A (enrdf_load_stackoverflow)
NL (1) NL6502190A (enrdf_load_stackoverflow)
NO (1) NO117494B (enrdf_load_stackoverflow)
SE (1) SE352531B (enrdf_load_stackoverflow)

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3486951A (en) * 1967-06-16 1969-12-30 Corning Glass Works Method of manufacturing semiconductor devices
US3524756A (en) * 1967-05-29 1970-08-18 Colorcon Process of coating tablets with alternate tacky and non-tacky layers
US3539380A (en) * 1968-01-08 1970-11-10 Upjohn Co Methylcellulose and polyalkylene glycol coating of solid medicinal dosage forms
US3900583A (en) * 1971-08-10 1975-08-19 American Home Prod Contoured belt coating method
US3919436A (en) * 1971-09-27 1975-11-11 Eisai Co Ltd Process for preparation of coated medicines
US4001390A (en) * 1974-04-04 1977-01-04 Shin-Etsu Chemical Co., Ltd. Method of coating pharmaceutical solid dosage forms
US4140756A (en) * 1976-06-10 1979-02-20 Mead Johnson & Company Film-coated matrix core tablet
US4302440A (en) * 1980-07-31 1981-11-24 Sterling Drug Inc. Easily-swallowed, powder-free and gastric-disintegrable aspirin tablet thinly-coated with hydroxypropyl methylcellulose and aqueous spray-coating preparation thereof
US4421738A (en) * 1979-07-31 1983-12-20 Eisai Co., Ltd. Sugar-coated tablet containing fat-soluble pharmaceutical material
US4508702A (en) * 1982-06-14 1985-04-02 Key Pharmaceuticals, Inc. Sustained release aspirin
US4555399A (en) * 1983-11-18 1985-11-26 Key Pharmaceuticals, Inc. Aspirin tablet
US4795032A (en) * 1987-12-04 1989-01-03 S. C. Johnson & Son, Inc. Wash-added, rinse-activated fabric conditioner and package
US4897270A (en) * 1985-09-30 1990-01-30 Glaxo Group Limited Pharmaceutical compositions
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US5122385A (en) * 1989-07-31 1992-06-16 Miles Inc. Method for producing a shine coating by aqueous spraying and flash drying
US6733780B1 (en) 1999-10-19 2004-05-11 Genzyme Corporation Direct compression polymer tablet core
US20050260236A1 (en) * 1999-10-19 2005-11-24 Geltex Pharmaceuticals, Inc. Direct compression polymer tablet core
US20060177415A1 (en) * 2004-11-01 2006-08-10 Burke Steven K Once a day formulation for phosphate binders
US20060251614A1 (en) * 2004-11-01 2006-11-09 Genzyme Corporation Aliphatic amine polymer salts for tableting
US20090047233A1 (en) * 2005-09-02 2009-02-19 Genzyme Corporation Method for removing Phosphate and Polymer Used Therefore
US20100093857A1 (en) * 2006-12-14 2010-04-15 Genzyme Corporation Amido-amine polymer compositions
US20100124542A1 (en) * 2006-07-18 2010-05-20 Genzyme Corporation Amine dendrimers
US20100129309A1 (en) * 2007-02-23 2010-05-27 Dhal Pradeep K Amine polymer compositions
US20100166696A1 (en) * 2007-04-27 2010-07-01 Dhal Pradeep K Amido-amine dendrimer compositions
US20100196305A1 (en) * 2007-03-08 2010-08-05 Dhal Pradeep K Sulfone polymer compositions
US20100254935A1 (en) * 2006-05-05 2010-10-07 Genzyme Corporation Amine condensation polymers as phosphate sequestrants
US20100316589A1 (en) * 2007-12-14 2010-12-16 Hitesh Bhagat Coated Pharmaceutical Compositions
US8425887B2 (en) 2006-09-29 2013-04-23 Genzyme Corporation Amide dendrimer compositions
US9585911B2 (en) 2005-09-15 2017-03-07 Genzyme Corporation Sachet formulation for amine polymers

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173626A (en) 1978-12-11 1979-11-06 Merck & Co., Inc. Sustained release indomethacin
DE3236192A1 (de) 1982-09-30 1984-04-05 Dr. Karl Thomae Gmbh, 7950 Biberach Gesteuertes und geregeltes verfahren zum vollautomatischen, kontinuierlichen dragieren
CA2349700A1 (en) 1998-11-12 2000-05-18 Merck & Co., Inc. Therapeutic polymorphs of a gaba-a alpha-5 inverse agonist and pamoate formulations of the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA652743A (en) * 1962-11-20 Charles E. Frosst And Co. Film coating for tablets
US3112220A (en) * 1960-02-26 1963-11-26 Abbott Lab Method and apparatus for coating particles
US3141792A (en) * 1961-09-10 1964-07-21 Ciba Geigy Corp Automatic tablet coating apparatus
US3256111A (en) * 1964-12-04 1966-06-14 Abbott Lab Method for coating tablets

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA652743A (en) * 1962-11-20 Charles E. Frosst And Co. Film coating for tablets
US3112220A (en) * 1960-02-26 1963-11-26 Abbott Lab Method and apparatus for coating particles
US3141792A (en) * 1961-09-10 1964-07-21 Ciba Geigy Corp Automatic tablet coating apparatus
US3256111A (en) * 1964-12-04 1966-06-14 Abbott Lab Method for coating tablets

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3524756A (en) * 1967-05-29 1970-08-18 Colorcon Process of coating tablets with alternate tacky and non-tacky layers
US3486951A (en) * 1967-06-16 1969-12-30 Corning Glass Works Method of manufacturing semiconductor devices
US3539380A (en) * 1968-01-08 1970-11-10 Upjohn Co Methylcellulose and polyalkylene glycol coating of solid medicinal dosage forms
US3900583A (en) * 1971-08-10 1975-08-19 American Home Prod Contoured belt coating method
US3919436A (en) * 1971-09-27 1975-11-11 Eisai Co Ltd Process for preparation of coated medicines
US4001390A (en) * 1974-04-04 1977-01-04 Shin-Etsu Chemical Co., Ltd. Method of coating pharmaceutical solid dosage forms
US4140756A (en) * 1976-06-10 1979-02-20 Mead Johnson & Company Film-coated matrix core tablet
US4421738A (en) * 1979-07-31 1983-12-20 Eisai Co., Ltd. Sugar-coated tablet containing fat-soluble pharmaceutical material
US4302440A (en) * 1980-07-31 1981-11-24 Sterling Drug Inc. Easily-swallowed, powder-free and gastric-disintegrable aspirin tablet thinly-coated with hydroxypropyl methylcellulose and aqueous spray-coating preparation thereof
US4508702A (en) * 1982-06-14 1985-04-02 Key Pharmaceuticals, Inc. Sustained release aspirin
US4555399A (en) * 1983-11-18 1985-11-26 Key Pharmaceuticals, Inc. Aspirin tablet
US4897270A (en) * 1985-09-30 1990-01-30 Glaxo Group Limited Pharmaceutical compositions
US4795032A (en) * 1987-12-04 1989-01-03 S. C. Johnson & Son, Inc. Wash-added, rinse-activated fabric conditioner and package
US4970008A (en) * 1988-12-20 1990-11-13 Kandathil Thomas V Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines
US5122385A (en) * 1989-07-31 1992-06-16 Miles Inc. Method for producing a shine coating by aqueous spraying and flash drying
US6733780B1 (en) 1999-10-19 2004-05-11 Genzyme Corporation Direct compression polymer tablet core
US20050260236A1 (en) * 1999-10-19 2005-11-24 Geltex Pharmaceuticals, Inc. Direct compression polymer tablet core
US9931358B2 (en) 1999-10-19 2018-04-03 Genzyme Corporation Direct compression polymer tablet core
US9579343B2 (en) 1999-10-19 2017-02-28 Genzyme Corporation Direct compression polymer tablet core
US8808738B2 (en) 2004-11-01 2014-08-19 Genzyme Corporation Aliphatic amine polymer salts for tableting
US7985418B2 (en) 2004-11-01 2011-07-26 Genzyme Corporation Aliphatic amine polymer salts for tableting
US20060177415A1 (en) * 2004-11-01 2006-08-10 Burke Steven K Once a day formulation for phosphate binders
US9895315B2 (en) 2004-11-01 2018-02-20 Genzyme Corporation Aliphatic amine polymer salts for tableting
US20060251614A1 (en) * 2004-11-01 2006-11-09 Genzyme Corporation Aliphatic amine polymer salts for tableting
US9555056B2 (en) 2004-11-01 2017-01-31 Genzyme Corporation Aliphatic amine polymer salts for tableting
US20090047233A1 (en) * 2005-09-02 2009-02-19 Genzyme Corporation Method for removing Phosphate and Polymer Used Therefore
US8986669B2 (en) 2005-09-02 2015-03-24 Genzyme Corporation Method for removing phosphate and polymer used therefore
US9585911B2 (en) 2005-09-15 2017-03-07 Genzyme Corporation Sachet formulation for amine polymers
US20100254935A1 (en) * 2006-05-05 2010-10-07 Genzyme Corporation Amine condensation polymers as phosphate sequestrants
US20100124542A1 (en) * 2006-07-18 2010-05-20 Genzyme Corporation Amine dendrimers
US8900560B2 (en) 2006-09-29 2014-12-02 Genzyme Corporation Amide dendrimer compositions
US9066972B2 (en) 2006-09-29 2015-06-30 Genzyme Corporation Amide dendrimer compositions
US8425887B2 (en) 2006-09-29 2013-04-23 Genzyme Corporation Amide dendrimer compositions
US8889738B2 (en) 2006-12-14 2014-11-18 Genzyme Corporation Amido-amine polymer compositions
US20100093857A1 (en) * 2006-12-14 2010-04-15 Genzyme Corporation Amido-amine polymer compositions
US8163799B2 (en) 2006-12-14 2012-04-24 Genzyme Corporation Amido-amine polymer compositions
US20100129309A1 (en) * 2007-02-23 2010-05-27 Dhal Pradeep K Amine polymer compositions
US20100196305A1 (en) * 2007-03-08 2010-08-05 Dhal Pradeep K Sulfone polymer compositions
US20100166696A1 (en) * 2007-04-27 2010-07-01 Dhal Pradeep K Amido-amine dendrimer compositions
US20100316589A1 (en) * 2007-12-14 2010-12-16 Hitesh Bhagat Coated Pharmaceutical Compositions

Also Published As

Publication number Publication date
BR6566503D0 (pt) 1973-07-17
ES312253A1 (es) 1966-02-16
GB1059508A (en) 1967-02-22
FR1455065A (fr) 1966-10-14
NO117494B (enrdf_load_stackoverflow) 1969-08-18
SE352531B (enrdf_load_stackoverflow) 1973-01-08
BE661581A (enrdf_load_stackoverflow) 1965-09-24
IL22778A (en) 1968-08-22
NL6502190A (enrdf_load_stackoverflow) 1965-10-18
DE1492029A1 (de) 1969-02-20

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